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Selecting Enterprise Email Security: the Buying Process

By Mike Rothman

To wrap up this series we will bring you through a process of narrowing down the shortlist and then testing products and/or services in play. With email it’s less subjective because malicious email is… well, malicious. But given the challenges of policy management at scale (discussed in our last post), you’ll want to ensure a capable UX and sufficient reporting capabilities as well.

Let’s start with the first rule of buying anything: you drive the process. You’ll have vendors who want you to use their process, their RFP/RFP language, their PoC guide, and their contract language. All that is good and well if you want to buy their product. But what you want is the best product to solve your problems, which means you need to drive your selection process.

We explained in our introduction that a majority of attacks start with a malicious email. So selecting the best platform remains critical for enterprises. You want to ensure your chosen vendor addresses the email-borne threats of not just today, but tomorrow as well.

A simple fact of the buying process is that no vendor ever says “We’re terrible at X, but you should buy us because Y is what’s most important to you.” Even though they should. It’s up to you to figure out each vendor’s real strengths and weaknesses and line them up against your requirements. That’s why it’s critical to have a firm handle on your requirements before you start talking to vendors.

The first step is to define your short list of 2-3 vendors who appear to meet your needs. You accomplish this by talking to folks on all sides of the decision. Start with vendors but also talk to friends, third parties (like us), and possibly resellers or managed service providers. When meeting vendors stay focused on how their tool addresses your current threats and their expectations for the next wave of email attacks. Make any compliance or data protection issues (or both) very clear because they drive the architecture and capabilities you need to test.

Don’t be afraid to go deep with vendors. You will spend a bunch of time testing platforms, so you should ask every question you can to make an educated decision. The point of the short list is to disqualify products that won’t work early in the process so you don’t waste time later.

Proof of Concept

Once you have assembled the short list it’s time to get hands-on with the email security platforms and run each through its paces through a Proof of Concept (PoC) test. The proof of concept is where sales teams know they have a chance to win or lose, so they bring their best and brightest. They raise doubts about competitors and highlight their own capabilities and successes. They have phone numbers for customer references handy. But forget all that now. You are running this show, and the PoC needs to follow your script – not theirs.

Preparation

Vendors design PoC processes to highlight their product strengths and hide weaknesses. Before you start any PoC be clear about the evaluation criteria. Your criteria don’t need to be complicated. Your requirements should spell out the key capabilities you need, with a plan to further evaluate each challenger based on squishier aspects such as set-up/configuration, change management, customization, user experience/ease of use, etc.

With email it all starts with accuracy. So you’ll want to see how well the email security platforms detect and block malicious email. Of course you could stop there and determine the winner based on who blocks 99.4%, which is better than 99.1%, right? Yes, we’re kidding. You also need to pay attention to manageability at scale.

The preparation involves figuring out the policies you’ll want to deploy on the product. These policies need to be consistent across all of the products and services you test. Here are some ideas on policies to think about:

  • Email routing
  • Blocked attacks (vs. quarantined)
  • Spam/phishing reporting
  • Email plug-in
  • Threat intelligence feeds to integrate
  • Disposition of email which violates policy
  • Attributes requiring email encryption
  • Integration with enterprise security systems: SIEM, SOAR, help desk

And we’re sure there are a bunch of other policy drivers we missed. Work with the vendor’s sales team to make sure you can exercise each product or service to its fullest capabilities. Make sure to track additional policies, above and beyond the policies you defined for all the competitors – you want an apples to apples comparison, but also want to factor in additional capabilities offered by any competitors.

One more thing: we recommend investing in screen capture technology. It is hard to remember what each tool did and how – especially after you have worked a few unfamiliar tools through the same paces. Capture as much video as you can of the user experience – it will come in handy as you reach the decision point.

Without further ado, let’s jump into the PoC.

Testing

Almost every email system (Exchange, Office 365, Google Suite, etc.) provides some means of blocking malicious email. So that is the base level for comparison. The next question becomes whether you want to take an active or passive approach during the PoC. In an active test you introduce malicious messages (known malware and phishing messages) into the environment to track whether the product or service catches messages which should be detected. A passive test uses the product against your actual mail stream, knowing it will get a bunch of spam, phishes, and attacks if you look at enough messages.

To undertake an active test you need access to these malicious messages, which isn’t a huge impediment as there are sites which provide known phishing messages, and plenty of places to get malware for testing. Of course you’ll want to take plenty of precautions to ensure you don’t self-inflict a real outbreak.

There is risk in doing an active test, but it enables you to evaluate false negatives (missing malicious messages), which create far more damage than false positives (flagging legitimate messages as malicious). Active versus passive remains a personal and cultural preference – every enterprise gets enough crap in their email to determine the effectiveness of an email security gateway without necessarily needing to introduce malware during testing.

So what does the test look like? Let’s say you are testing two email security services, Service A and Service B. You’d need to passively connect the service to the existing mail system to benchmark each service’s capabilities.

  1. Service A baseline: In a baseline test we see how Service A compares to your existing (or built-in) capabilities. You blind copy your entire mail stream to Gateway A to see how much junk it catches. That represents the value-add capabilities of Service A. This is a passive analysis, so the service is not blocking anything rather you’d see what it would block if it was deployed inline.
  2. Service B baseline: Like the previous test, blind copy the mail stream from your existing service through Gateway B and figure out how much junk it catches.

This testing approach requires a sufficient number of emails for a statistically significant sample to see the effectiveness of each service – especially given that each test will involve different messages. So you need to ensure enough time elapses for each service to see a similar number of malicious emails. How much time is that? It depends on your message volume and how many email attacks you see daily. But figure somewhere around two weeks for an enterprise, likely tens of millions of emails.

The vendor should be able to give you a report on the messages its service blocked and why. Remember that anything that the email security service would block represents a failure of the base platform (baseline). Especially if you do an active test, then you’ll know the gateway should have detected some messages. These tests make the value of the service clear pretty quickly.

You’ll also want to spot check quarantined messages to ensure the security service doesn’t generate too many false positives.

Don’t forget to test outbound messages for sensitive content, which requires a more active approach. You’ll want to test some messages with sensitive content, both in bodies and as attachments. We don’t recommend you actually put company secrets in test email, but you can put some test messages together to sensitive data.

Your admin team should grade each service for ease of use and managing malicious email, while memory is fresh and perceptions are raw, which means ask their opinions multiple times during the 2-3-week test. After spending a week or two with one service, they won’t remember what they liked and didn’t about earlier tests – another reason screen grabs are handy.

Given the importance of having employees use the security tools you give them, we suggest you pick a group of 15-20 employees to test user-oriented features, like installing an agent, reporting spam/phishing and quarantine. Quickly survey the test group to make sure the tool hits the mark in terms of effectiveness and user experience.

Postmortem

At the end of the test evaluate both successes and failures of the PoC in terms of your use cases and requirements. Given the dashboards and reports email security vendors provide, the relative effectiveness of each service should be reasonably clear. Of course vendors will want to walk you through the results to highlight how well their service performed. Sigh. But that’s part of the game, so you’ll need to sit around for an hour of wrap-up.

Documentation

The end goal is a recommendation, so you need to document what you think and then present it to secure funding. You may not be in the room when the final decision comes down, so your documentation must clearly articulate the reasons for your choice. We usually structure this artifact of the decision process as follows:

  • Requirements: Tell them what you need and who said you need it. This shouldn’t be new information but it’ll be a good refresher.
  • Coverage: What works and doesn’t with the desired solution within the context of your requirements, both now and as you envision them evolving. You want to make sure that your choice meets the requirements you just laid out.
  • Competition: What other vendors did you disqualify and why? What did you learn in the proof of concept? Are any of the competitors workable? Would you sacrifice any capabilities or features if another product was selected?
  • Cost estimate: What will it cost to move to the new platform? How much is a capital expense, and what fraction is operational? What kind of investment in professional services will be required?
  • Migration plan: What will migration entail? How long will it take? Will the migration disrupt service in any way?
  • Recommendation: Your entire document should be building to this point, where you put the best path down on paper. If it is a surprise to your audience, you did something wrong. This section is about telling them what they already know and making sure they have an opportunity to ask any remaining questions.

Now you have the thumbs up from the internal team (we hope!) You need to negotiate with the vendor and get the deal done. We won’t get into the specifics of negotiating (you likely have people to do that), but you can use time-honored tactics like waiting until the end of the quarter, playing one vendor against another (if either could meet your requirements), and possibly asking for non-cash add-ons (such as professional services or product modules).

Migration

As you wrap up the buying process, let’s step back for a moment to focus on what’s important: getting stuff done as simply and efficiently as possible. The good news is that migration to a new enterprise security email service should go smoothly because you’ve already run email through it during PoC. It’s just a matter of putting the winning service back inline and blocking the bad stuff (both inbound and outbound).

We recommend you do monthly check-ins with your vendor account team for at least the first six months. Are you getting the value you expected? What’s working well and what’s not, especially now with a real production environment. You can go to quarterly check-ins once everything is working as advertised.

Around the time you feel comfortable with the system, you can bring up the adjacent services discussed in our last post with your vendor, such as security awareness training, DNS, and archiving/eDiscovery. Walk before you think about running – get your base capabilities in place and working well, and then start thinking about how you can add value to your email security platform.

With that you should have a good sense of how to select your next enterprise email security platform. We will package this up as a white paper over the next few weeks, so keep an eye out for in our research library later this year.

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